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Reaction of ethyl α, β-unsaturated α- or β-nitrocarboxylates with sodium azide

✍ Scribed by Chung-gi Shin; Yasuchika Yonezawa; Juji Yoshimura

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
163 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

Although many literatures have been published on the synthesis and chemistry of azide compounds, the synthetic route to a,@-unsaturated a-and S-azidocarboxylic esters (1 and 4) has not been extended beyond the following methods: methyl a-azidocinnamates were synthesized by condensation of methyl azidoacetate and arylaldehydes') and methyl a-azidopropenoate and methyl S-azidocinnamate by addi-

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Treatment of c~-silyl-cc,[~-unsaturated enones, readily preparable as regio-and stereodefined compounds in high yields, with either 2 equiv, oflCl or one equiv, each oflC1 and A1C13 provides the corresponding cc-iodo-a,[3unsaturated enones in high yields.